Rings Bonded Directly To Each Other In Acid Moiety Patents (Class 560/102)
-
Patent number: 5378396Abstract: A liquid crystal compound represented by formula (I) ##STR1## wherein R denotes a linear alkyl group having 6 to 14 carbon atoms, X denotes a single bond or an oxygen atom, K and L are independently 1 or 2, n is an integer of 3 to 8, and C* denotes an asymmetric carbon atom.and a liquid crystal display device formed therefrom.Type: GrantFiled: April 22, 1994Date of Patent: January 3, 1995Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Tomoyuki Yui, Toshio Watanabe, Yoshihisa Arai, Masahiro Johno
-
Patent number: 5374376Abstract: Disclosed are herein optically active aromatic compounds represented by the formula (I): ##STR1## wherein X represents --COO-- or --OCO--; Y represents --COO--, --OCO-- or --O--; R.sub.2 represents an alkyl or alkoxyalkyl group having 1 to 20 carbon atoms unsubstituted or substituted by a halogen atom; R.sub.1 represents an alkyl group having 3 to 20 carbon atoms;Z represents ##STR2## wherein p represents a number of 1 to 5 and * indicates an asymmetric carbon atom; l and k each represents a number of 1 or 2; m and s each represents a number of 0 or 1, which are useful as a liquid crystal.Type: GrantFiled: September 21, 1993Date of Patent: December 20, 1994Assignee: Sumitomo Chemical Company, LimitedInventors: Takayuki Higashii, Isao Kurimoto, Shoji Toda, Masayoshi Minai, Shigeaki Chika, Koichi Fujisawa, Kiyoshi Imamura
-
Patent number: 5374375Abstract: A liquid crystal compound represented by formula (I), ##STR1## wherein A represents --C.sub.3 H.sub.7, --C.sub.4 H.sub.9 or --C.sub.8 H.sub.17 ; when A is --C.sub.3 H.sub.7, m is an integer of 8, 10, 12 or 14; and when A is --C.sub.4 H.sub.9 or --C.sub.8 H.sub.17, m is an integer of 7 to 14,said compound having an antiferroelectric phase.Type: GrantFiled: June 26, 1992Date of Patent: December 20, 1994Assignee: Mitsubishi Gas Chemical Co., Inc.Inventors: Tomoyuki Yui, Masahiro Johno, Toshio Watanabe, Masamichi Mizukami, Yoshihisa Arai
-
Patent number: 5364560Abstract: An antiferroelectric liquid crystal compound which is a compound represented by ##STR1## wherein R denotes a linear aliphatic alkyl group having 6 to 14 carbon atoms; A denotes a single bond or an oxygen atom; X and Y independently denote a hydrogen atom or a fluorine atom but they are not hydrogen atoms at the same time; h and i are independently 1 or 2; m is an integer of 3 to 10; Z denotes CH.sub.3, C.sub.2 H.sub.5 or CF.sub.3 ; k is 0 or an integer of 5 to 8; l is 0 or 1; n is an integer of 1 to 6; W denotes CH.sub.3 or CF.sub.3 ; when W is CH.sub.3, p and q are both 0 and r is 8; when W is CF.sub.3, p is 5 to 8, q is 1 and r is 1 to 4; and C* denotes an asymmetric carbon atom,and a liquid crystal display device using same.Type: GrantFiled: January 29, 1992Date of Patent: November 15, 1994Assignee: Mitsubishi Gas Chemical Co., Inc.Inventors: Masamichi Mizukami, Tomoyuki Yui, Masahiro Johno, Yoshihisa Arai, Hiroshi Mineta
-
Patent number: 5362822Abstract: An adduct is prepared by reacting (A) a compound containing at least one epoxy group per molecule, with (B) a compound containing at least one epoxide reactive group per molecule selected from the group consisting of phenolic, thiol, secondary amine and carboxyl; wherein (i) when compound (A) is a polyepoxide, compound (B) contains a single epoxide reactive group per molecule; (ii) when compound (A) is a monoepoxide it is a monoglycidyl ether and compound (B) contains at least two epoxide reactive groups per molecule; and (iii) at least one of components (A) and (B) contains a rodlike mesogenic moiety. These adducts are useful in the preparation of polyurethanes.Type: GrantFiled: January 3, 1994Date of Patent: November 8, 1994Assignee: The Dow Chemical CompanyInventor: Robert E. Hefner, Jr.
-
Patent number: 5354511Abstract: Compounds having non-linear optical activity of the general formula ##STR1## wherein D and A are electron donor and acceptor groups, respectively, R.sup.1 and R.sup.2 are aromatic bridging groups, X and Y are preferably groups capable of partaking in polymerization reactions are suitable for use in polymer-based light modulator devices.Type: GrantFiled: November 27, 1992Date of Patent: October 11, 1994Assignee: AlliedSignal Inc.Inventors: Chengjiu Wu, Jianhui Shan, Ajay Nahata
-
Patent number: 5352822Abstract: The present invention discloses pesticidally active compounds of formula (II) ##STR1## or a salt thereof, wherein Q is an monocyclic aromatic ring, or fused bicyclic ring system of which at least one ring is aromatic containing 9 or 10 atoms of which one may be nitrogen and the rest carbon each ring system being optionally substituted, or Q is a dihalovinyl group or a group R.sup.6 --C.tbd.C-- where R.sup.6 is C.sub.1-4 alkyl, tri C.sub.1-4 alkylsilyl, halogen or hydrogen; R.sup.2, R.sup.3 , R.sup.4 and R.sup.5 are the same or different with at least one being hydrogen and the others being independently selected from hydrogen, halo, C.sub.1-4 alkyl or C.sub.1-4 haloalkyl; and R.sup.1 is selected from hydrogen and C.sub.1-8 hydrocarbyl optionally substituted by dioxalanyl, halo, cyano, trifluoromethyl, trifluoromethylthio or C.sub.1-6 alkoxy and X.sup.1 is hydrogen, fluoro or chloro.Type: GrantFiled: April 7, 1993Date of Patent: October 4, 1994Assignee: Roussel UclafInventors: Robert J. Blade, George S. Cockerill, John E. Robinson
-
Patent number: 5334327Abstract: Novel compounds of formula (I), in which R is R.sup.1, R.sup.1 O or R.sup.1 COO, where R.sup.1 is C.sub.1-12 alkyl, n and m are 0 or 1 provided that (n+m) is 0 or 1, each of a, b, c and d are independently 0 or 1, provided (a+b+c+d) is not zero, but excluding the case where a and b are 0 and m is 0 and one of c or d is 0 are described, being useful constituents of nematic liquid crystal materials.Type: GrantFiled: May 12, 1992Date of Patent: August 2, 1994Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and North IrelandInventors: George W. Gray, David Lacey, Kenneth J. Toyne, Michael Hird, Damien G. McDonnell
-
Patent number: 5328643Abstract: The invention relates to optically active compounds represented by the general formula I ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, Q.sub.1, Q.sub.2, Q.sub.3, and M are defined as in the specification, methods and intermediates for their preparation, liquid crystal compositions comprising at least one optically active compound of formula I and their use in electrooptical display, switching and modulation devices.Type: GrantFiled: February 26, 1992Date of Patent: July 12, 1994Assignees: Takeda Chemical Industries, Ltd., Hitachi, Ltd.Inventors: Yuka Sudo, Katsumi Kondo, Teruo Kitamura, Koichi Matsumura, Mitsuru Kawada, Yoshihiro Sugihara
-
Patent number: 5324451Abstract: A compound represented by formula (I): ##STR1## wherein R.sub.1 represents an alkyl group having from 1 to 18 carbon atoms; R.sub.2 represents an alkyl group having from 2 to 16 carbon atoms; rings A, B, C, and D each represents a 1,4-phenylene group or a 1,4-phenylene group having one or two halogen atoms; Y represents a single bond, ##STR2## m and n each represents 0 or 1; p represents 0, 1, or 2; q represents 0 or an integer of from 1 to 6; and C* and C** each represents an asymmetric carbon atom in an (S)- or (R)-configuration, and a liquid crystal composition containing the compound of formula (I). The compound of formula (I) is a chiral liquid crystal compound exhibiting large spontaneous polarization, a long helical pitch, an SC* phase in a broad temperature range including room temperature, satisfactory orientation, and a high rate of response.Type: GrantFiled: April 20, 1992Date of Patent: June 28, 1994Assignees: Dainippon Ink and Chemicals, Inc., Kawamura Institute of Chemical ResearchInventors: Sadao Takehara, Tadao Shoji, Hiroshi Ogawa, Toru Fujisawa, Masashi Osawa
-
Patent number: 5312814Abstract: .alpha.- Phosphonocarboxylate compounds are provided which inhibit the enzyme squalene synthetase and thereby inhibit cholesterol biosynthesis. These compounds have the formula ##STR1## wherein R.sup.1 is a lipophilic group which contains at least 7 carbons and is substituted alkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted arylalkyl or optionally substituted aryl;Z is H, halogen, hydroxy, hydroxyalkyl or lower alkyl;R.sup.2 and R.sup.3 are independently H, metal ion or other pharmaceutically acceptable cation, or a prodrug ester;R.sup.4 is H, metal ion or other pharmaceutically acceptable cation, lower alkyl, lower alkenyl, arylalkyl, aryl or a prodrug ester.Type: GrantFiled: December 9, 1992Date of Patent: May 17, 1994Assignee: Bristol-Myers Squibb Co.Inventors: Scott A. Biller, David R. Magnin
-
Patent number: 5312564Abstract: A novel optically active liquid crystal compound and a liquid crystal composition containing the same are provided, which compound is expressed by the formula ##STR1## wherein R.sub.1 is alkyl or alkoxy of 4-18 C; R.sub.2 is alkyl, alkoxy, acyl or alkoxymethyl of 4-18C; but either one of R.sub.1 or R.sub.2 is an optically active group; either one of X.sub.1 or X.sub.2 is halogen atom and the other is H; m and n each are 0 or 1 and m+n is 0 or 1.Type: GrantFiled: December 31, 1992Date of Patent: May 17, 1994Assignee: Chisso CorporationInventors: Kazutoshi Miyazawa, Hiromichi Inoue, Shinichi Saito, Takashi Inukai, Kanetsugu Terashima, Mitsuyoshi Ichihashi
-
Patent number: 5312958Abstract: A process for the production of a compound of general formula ##STR1## wherein R represents cyano, carboxy which may be esterified or amidated or tetrazolyl which may be substituted, comprising brominating the corresponding methyl compound with a brominating agent such as N -bromoacetamide, N-bromophtalimide, N-bromosuccinimide and so on in a halogenated hydrocarbon solvent in the presence of an azobis compound.Type: GrantFiled: January 26, 1993Date of Patent: May 17, 1994Assignee: Takeda Chemical Industries, Ltd.Inventors: Syuji Suenaga, Hitoshi Kawaguchi, Takeshi Kato
-
Patent number: 5302751Abstract: A process is disclosed that is useful for separating the enantiomers of a racemic mixture of an aliphatic carboxylic acid having the formula ##STR1## where R.sub.1 is hydrogen or alkyl, R.sub.2, R.sub.3 and R.sub.4 are independently different and are hydrogen, alkyl, cycloalkyl, alkenyl, alkynyl, phenyl, substituted phenyl, naphthyl, substituted naphthyl, heteroaryl, substituted heteroaryl, haloalkyl, alkoxyalkyl, alkylthioalkyl, phenylalkyl, substituted phenylalkyl, heteroalkylalkyl, substituted heteroalkylalkyl or cycloalkylalkyl.Type: GrantFiled: January 21, 1992Date of Patent: April 12, 1994Assignee: Ethyl CorporationInventors: Thanikavelu Manimaran, Alicia A. Potter
-
Patent number: 5300668Abstract: 1-[4'-(2"-Ethyl-5",7"-dimethylimidazo[4,5-b]pyridin-3-yl)methylphenyl]cyclo pent-3-ene-1-carboxylic acid and its pharmaceutically acceptable salts inhibit angiotensin II in mammals and are useful in treating conditions such as hypertension, congestive heart failure and glaucoma and as the active ingredient in pharmaceutical compositions for treating such conditions.Type: GrantFiled: March 10, 1993Date of Patent: April 5, 1994Assignee: Pfizer Inc.Inventor: Paul A. Dasilva Jardine
-
Patent number: 5296601Abstract: A process for producing a carboxylic acid ester, which comprises reacting an organic chloride having at least one chlorine atom on its ring of a substituted or unsubstituted, aromatic or heterocyclic hydrocarbon with carbon monoxide and an amine or an alcohol in the presence of a base by using as catalysts a palladium compound and a phosphine compound represented by the general formula (V):(R).sub.2 P--X--P(R).sub.2 (V)wherein R is an alkyl group or a substituted or unsubstituted phenyl group, and X is an alkylene group having 1 to 6 carbon atoms, ##STR1## or a binaphthyl group.Type: GrantFiled: May 27, 1992Date of Patent: March 22, 1994Assignee: Nihon Nohyaku Co., Ltd.Inventors: Keiji Suto, Masaaki Kudo, Moriharu Yamamoto
-
Patent number: 5294366Abstract: In accordance with the present invention, there are provided carboxylate compounds and liquid compositions thereof represented by the following formula (A) ##STR1## wherein R.sup.1 represents one group selected from the group consisting of alkyl group having 6 to 18 carbon atoms, alkoxy group having 6 to 18 carbon atoms and halogenated alkyl group of 6 to 18 carbon atoms, C* represents an asymmetric carbon atom, and R.sup.2 represents a group represented by the following formula (A)--(CH.sub.2).sub.m --CH.sub.3 or (B)--(CH.sub.2).sub.n --COOR.sub.3 wherein m represents an integer of 2 to 6, n represents an integer of 0 to 5, and R.sup.3 represents alkyl group having 1 to 10 carbon atoms.Type: GrantFiled: September 4, 1991Date of Patent: March 15, 1994Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Toyozi Shimizu, Hideo Yamaoka, Shinichi Nishiyama, Shoichi Miyakoshi, Tooru Yamanaka, Nobuyuki Doi
-
Patent number: 5278338Abstract: A method for racemizing an optically active carboxylic acid, or ester thereof, of the formula: ##STR1## where R.sub.1 is hydrogen, hydroxy, halo, cyano, C.sub.1 to C.sub.6 linear or branched alkoxy, amino or substituted amino or the group ##STR2## is nitrile; R.sub.2, R.sub.3 and R.sub.4 are different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, C.sub.1 to C.sub.6 linear or branched haloalkyl, aralkyl, cycloalkyl, alkyl substituted cycloalkyl, C.sub.6 to C.sub.10 aryl, C.sub.1 to C.sub.6 linear or branched alkoxy, C.sub.6 to C.sub.10 aryloxy, C.sub.1 to C.sub.6 alkylthio, C.sub.3 to C.sub.8 cycloalkylthio, C.sub.6 to C.sub.10 arylthio, C.sub.6 to C.sub.10 arylcarbonyl, C.sub.4 to C.sub.8 cycloalkenyl, trifluoromethyl, halo, C.sub.4 to C.sub.5 heteroaryl, C.sub.10 to C.sub.14 aryl, or biphenyl unsubstituted or substituted with methyl or halo, comprising heating said optically active carboxylic acid or ester thereof in the presence of water at a temperature of from about 40.degree. C.Type: GrantFiled: November 4, 1992Date of Patent: January 11, 1994Assignee: Ethyl CorporationInventor: Rhonda L. Trace
-
Patent number: 5278333Abstract: A process for the .alpha.-monoalkylation of arylacetonitriles, arylacetoesters and arylacetic acids with dialkyl carbonates in liquid phase, in the presence of bases at temperatures ranging from about 100.degree. C. to about 270.degree. C.Type: GrantFiled: July 30, 1992Date of Patent: January 11, 1994Assignee: Tessenderlo Chemie N.V.Inventors: Pierre C. Loosen, Pietro Tundo, Maurizio Selva
-
Patent number: 5271864Abstract: Ferroelectric liquid crystal compounds and compositions containing cyclohexenyl derivatives are provided. Specifically provided are compounds of formula: ##STR1## wherein R.sub.1 and R.sub.2 can be an alkyl, cycloalkyl, alkenyl, alkoxy, thioalkyl, alkylsilyl group having from one to about twenty carbon atoms. Y denotes --COO--, --OOC--, --CH.sub.2 O--, or --OCH.sub.2 --; and Ar.sub.1 and Ar.sub.2, independently of one another, can be selected from the group consisting of phenyl rings, halogenated phenyl rings and nitrogen-containing aromatic groups. In preferred embodiments the compounds of this invention contain at least one nitrogen-containing aromatic ring. Ar.sub.1 and Ar.sub.2 can be selected from 1,4-phenyl, mono- or dihalogenated 1,4-phenyl, 2,5-pyridinyl, 2,5-pyrimidyl, 2,5-pyrazinyl, 2,5-thiadiazole, 3,6-pyridazinyl and 1,4-cyclohexyl either or both be chiral racemic groups or chiral nonracemic groups.Type: GrantFiled: August 7, 1992Date of Patent: December 21, 1993Assignee: Displaytech, Inc.Inventors: Michael D. Wand, Rohini T. Vohra, Kundalika M. More, William N. Thurmes
-
Patent number: 5264152Abstract: An optically active compound represented by the formula (I): ##STR1## wherein R is a straight or branched chain alkyl or alkoxy group having 1 to 15 carbon atoms, ##STR2## is a 1,4-cyclohexylene or 1,4-phenylene group, ##STR3## is a 1,4-phenylene or 3-fluoro-1,4-phenylene group, X is a mono-, di- or tri-fluoromethyl group, W is a straight or branched chain or cyclic alkylene group having 1 to 16 carbon atoms or a straight or branched chain alkenylene group having 2 to 16 carbon atoms, Y is a bond or --COO--, and Z is a straight or branched chain alkyl group having 1 to 8 carbon atoms, a phenyl group or a hydrogen atom, which is useful as a component of ferroelectric liquid crystal compositions or as a device utilizing said composition.Type: GrantFiled: April 7, 1992Date of Patent: November 23, 1993Assignee: Sharp Kabushiki KaishaInventors: Makoto Shiomi, Mitsuhiro Koden, Tomoaki Kuratate, Fumiaki Funada
-
Patent number: 5262086Abstract: (R)- and (S)-enantiomer composition represented by the formula (I) having sufficient high optical purity for exhibiting optically tristable states in S*(3) phase; ##STR1## wherein Ra means a C.sub.5 -C.sub.14 alkyl group or a C.sub.5 -C.sub.14 alkoxy group, preferably a C.sub.5 -C.sub.14 alkyl group, Rb means a C.sub.4 -C.sub.12 normal alkyl group or a C.sub.4 -C.sub.12 branched alkyl group, X means a ##STR2## group or a ##STR3## group, Z means a fluorine containing alkyl group, preferably a trifluoromethyl group and * shows an optically active carbon.Type: GrantFiled: June 26, 1992Date of Patent: November 16, 1993Assignee: Showa Shell Sekiyu Kabushiki KaishaInventors: Yoshiichi Suzuki, Horiyuki Mogamiya, Ichiro Kawamura
-
Patent number: 5262085Abstract: Trifluoromethylene compounds of the formula I ##STR1## which can be used as components of liquid-crystalline media for liquid-crystal and electrooptical display elements.Type: GrantFiled: July 19, 1991Date of Patent: November 16, 1993Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Ekkehard Bartmann, Eike Poetsch, Ulrich Finkenzeller, Herbert Plach
-
Patent number: 5260285Abstract: Novel substituted imidazopyridazines of formula (I) which are useful as angiotensin II antagonists, are disclosed.Type: GrantFiled: November 25, 1991Date of Patent: November 9, 1993Assignee: Merck & Co., Inc.Inventors: Eric E. Allen, William J. Greenlee, Prasun K. Chakravarty, Malcolm MacCoss, Arthur A. Patchett, Thomas F. Walsh
-
Patent number: 5238598Abstract: Disclosed in the present invention are the optically active aromatic compounds having a trifluoromethyl group useful as a component of ferroelectric liquid crystal compositions, a process for preparing the above compounds, liquid crystal compositions having the above compounds as an active ingredient, and liquid crystal elements using the above compositions. The optically active aromatic compounds of the Present invention represented by the formula: ##STR1## have the very excellent properties as a liquid crystal material and are useful for the preparation of liquid crystal compositions and the liquid crystal elements using such compositions.Type: GrantFiled: December 13, 1990Date of Patent: August 24, 1993Assignee: Sumitomo Chemical Company, LimitedInventors: Isao Kurimoto, Takayuki Higashii, Shoji Toda, Masayoshi Minai, Chizu Sekine, Takeshi Tani, Koichi Fujisawa
-
Patent number: 5238602Abstract: Compounds of the formula ##STR1## wherein n stands for the number 0 or 1; the rings A.sup.1, A.sup.2 and A.sup.3 represent 1,4-phenylene, 2-fluoro-1,4-phenylene or trans-1,4-cyclohexylene or one of these rings also represents a 2,5-disubstituted pyrimidine ring or a trans-2,5-disubstituted m-dioxane ring; X.sup.1 represents a single covalent bond, --COO--, --OOC--, --CH.sub.2 CH.sub.2 --, p--C.sub.6 H.sub.4 --, --CH.sub.2 CH.sub.2 --p-- C.sub.6 H.sub.4 --, --CH.sub.2 CH.sub.2 --p--C.sub.6 H.sub.4 --CH.sub.2 CH.sub.2 -- or, insofar as the rings A.sup.1 and A.sup.2 represent 1,4-phenylene, also --NON--; R.sup.2 represents 1E-alkenyl, 2Z-alkenyl, 3E-alkenyl, 4-alkenyl or alkenyloxy, with the proviso that the oxygen atom in alkenyloxy is linked with a saturated carbon atom; and R.sup.1 signifies 1E-alkenyl, 2Z-alkenyl, 3E-alkenyl, 4-alkenyl or, insofar as R.sup.2 represents alkenyloxy, also alkyl, their manufacture, as well as liquid crystalline mixtures and the use for electro-optical purposes.Type: GrantFiled: May 26, 1987Date of Patent: August 24, 1993Assignee: Hoffmann La Roche Inc.Inventors: Martin Petrzilka, Martin Schadt
-
Patent number: 5236620Abstract: Derivatives of difluorobenzene of the formula IR.sup.1 --(--A.sup.o --).sub.m --Z.sup.1 --A.sup.1 --Z.sup.2 --A.sup.2 --R.sup.2 Iwherein R.sup.1, R.sup.2, A.sup.o, A.sup.1, A.sup.2, Z.sup.1, Z.sup.2 and m have the meaning indicated in patent claim 1, their preparation and their use as components of liquid-crystal media.Type: GrantFiled: May 15, 1989Date of Patent: August 17, 1993Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Volker Reiffenrath, Joachim Krause, Andreas Wachtler, Georg Weber, Thomas Geelhaar
-
Patent number: 5235101Abstract: An improved process for the separation of enantiomers of a mixture of certain aliphatic carboxylic acids or esters thereof is disclosed. The process involves adding an inert liquid to the reaction solution formed by: (i) forming a salt solution comprising said racemic mixture of a C.sub.1 to C.sub.6 linear or branched aliphatic carboxylic acid and an organic or inorganic base; (ii) treating said salt solution with less that equimolar equivalents of a chiral organic nitrogenous base; (iii) precipitating from the reaction solution formed in step (ii) the less soluble diastereomeric salt; (iv) addition of a countersolvent to the slurry formed in step (iii); (v) extracting the more soluble diastereomeric salt or the salt of carboxylic acid and the base added in step (i) into the countersolvent. The inert liquid and the countersolvent must be of sufficiently different density.Type: GrantFiled: January 24, 1992Date of Patent: August 10, 1993Assignee: Ethyl CorporationInventors: Deepak R. Patil, Azfar A. Choudhury, Abbas Kadkhodayan
-
Patent number: 5235095Abstract: An improved process for the separation of enantiomers of a racemic mixture of certain aliphatic carboxylic acids or esters thereof is disclosed. The process involves: (i) forming a salt solution comprising said racemic mixture of a C.sub.1 to C.sub.6 linear or branched aliphatic carboxylic acid and an organic or inorganic base; (ii) treating said salt solution with one-half molar equivalent of a chiral organic nitrogenous base having a base strength no stronger than said organic or inorganic base; and (iii) precipitating from the reaction solution formed in step (ii) the less soluble diastereomeric salt, the improvement being adding to the salt solution of step (ii) an inert organic or inorganic base that is soluble in the salt solution.Type: GrantFiled: January 24, 1992Date of Patent: August 10, 1993Assignee: Ethyl CorporationInventors: Abbas Kadkhodayan, Deepak R. Patil, Azfar A. Choudhury
-
Patent number: 5235100Abstract: A process for the separation of a racemic mixture of certain aliphatic carboxylic acids or esters thereof is disclosed. The process comprises:i) separating a racemic mixture of an aliphatic carboxylic acid or ester thereof having the formula: ##STR1## where R.sub.1 is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl; R.sub.2, R.sub.3 and R.sub.4 are different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl; cycloalkyl; alkyl-substituted cycloalkyl; C.sub.6 to C.sub.14 aryl; C.sub.1 to C.sub.6 alkylthio; C.sub.2 to C.sub.8 cycloalkylthio; C.sub.6 to C.sub.10 arylthio; C.sub.6 to C.sub.10 arylcarbonyl; C.sub.4 to C.sub.8 cycloalkenyl; trifluoromethyl; halo; or C.sub.4 to C.sub.Type: GrantFiled: January 24, 1992Date of Patent: August 10, 1993Assignee: Ethyl CorporationInventors: Azfar A. Choudhury, Abbas Kadkhodayan, Deepak R. Patil
-
Patent number: 5233075Abstract: A process comprising preparing an aromatic carboxylic ester and an alkyl iodide by carboxylating an aromatic iodide in the presence of an alkylating agent and a catalytic amount of a transition metal under aromatic carboxylic ester and alkyl iodide forming conditions of temperature, pressure and ultrasound.Type: GrantFiled: October 15, 1991Date of Patent: August 3, 1993Assignee: Eastman Kodak CompanyInventors: Guy R. Steinmetz, Andrew J. Matosky
-
Patent number: 5230830Type: GrantFiled: April 15, 1992Date of Patent: July 27, 1993Assignee: The Secrteary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern IrelandInventors: David Coates, Simon Greenfield, Ian C. Sage
-
Patent number: 5230827Abstract: Derivatives of 2,3-Difluorobenzoic acid compounds of the formula I ##STR1## in which R.sup.1 and R.sup.2, independently of one another, are each an alkyl group having 1 to 15 C atoms, in which, in addition, one or two non-adjacent CH.sub.2 groups may be replaced by --O--, --CO--, --CH.dbd.CH-- and/or --C.tbd.C--, andA.sup.1 and A.sup.2, independently of one another, are each 1,4-phenylene which is unsubstituted or substituted by one or two fluorine atoms, and in which, in addition, one or two CH groups may be replaced by N, or are trans1,4-cyclohexylene, or one of the two A.sup.1 and A.sup.2 groups is alternatively a single bond,are suitable as components of liquid-crystalline phases.Type: GrantFiled: May 12, 1989Date of Patent: July 27, 1993Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Volker Reiffenrath, Joachim Krause, Andreas Wachtler, Georg Weber, Thomas Geelhaar
-
Patent number: 5230826Abstract: Compounds of the formula ##STR1## wherein X.sup.1 denotes fluorine or chlorine and X.sup.2 denotes hydrogen, fluorine or chlorine; R.sup.1 is 3E-alkenyl, 4-alkenyl, 2E-alkenyloxy or 3-alkenyloxy; n stands for the number 0 or 1; one of the groups Y.sup.1 and Y.sup.2 is a single covalent bond, --COO--, --OOC--, --CH.sub.2 CH.sub.2 --, --CH.sub.2 O-- or --OCH.sub.2 -- and the other of the groups Y.sup.1 and Y.sup.2 is a single covalent bond; and rings A.sup.1 and A.sup.2 each individually are substituted or unsubstituted trans-1,4-cyclohexylene, in which optionally 2 non-adjacent CH.sub.2 groups are replaced by oxygen, or substituted or unsubstituted 1,4-phenylene, in which optionally 1 CH group or 2 CH groups is/are replaced by nitrogen; with the proviso that X.sup.2 denotes fluorine or chlorine and/or Y.sup.1 or Y.sup.2 denotes --CH.sub.2 O-- or --OCH.sub.2 -- when simultaneously X.sup.1 is fluorine and R.sup.1 is 3E-alkenyl,and their use for liquid crystalline mixtures and electro-optical purposes.Type: GrantFiled: October 26, 1988Date of Patent: July 27, 1993Assignee: Hoffmann-La Roche Inc.Inventors: Arthur Boller, Richard Buchecker, Martin Schadt, Alois Villiger
-
Patent number: 5220053Abstract: An improved process for the separation of enantiomers of a racemic mixture of certain aliphatic carboxylic acids or esters thereof is disclosed. The process involves adding a mixture of the aliphatic carboxylic acid to the material formed by: (i) forming a solution comprising said racemic mixture of a C.sub.1 to C.sub.6 linear or branched aliphatic carboxylic acid and an organic or inorganic solvent; (ii) treating said solution with a chiral organic nitrogenous base; (iii) precipitating from the reaction solution formed in step (ii) a crystalline material comprised of the less soluble diastereomeric salt. The solution is admixed with the crystalline material for a time sufficient to cause an increase in the amount of the less soluble diastereomeric salt in the crystalline material.Type: GrantFiled: January 24, 1992Date of Patent: June 15, 1993Assignee: Ethyl CorporationInventors: Azfar A. Choudhury, Abbas Kadkhodayan, Deepak R. Patil
-
Patent number: 5217644Abstract: A mesomorphic compound represented by the following formula (I): ##STR1## wherein R.sup.1 denotes analkyl group having 1-18 carbon atoms; R.sup.2 denotes an alkyl group having 1-12 carbon atoms; A and B respectively denote ##STR2## Z.sup.1 and Z.sup.2 respectively denote --H, 'CH.sub.3, --OCH.sub.3, --CN or halogen; m and n respectively denote 0, 1 or 2 and p denotes 1 or 2 with proviso that m+n+p =2 or 3; X denotes a single bond, ##STR3## denotes an asymmetric carbon atom.Type: GrantFiled: January 29, 1991Date of Patent: June 8, 1993Assignee: Canon Kabushiki KaishaInventors: Hiroyuki Nohira, Yoko Yamada, Shinichi Nakamura, Akira Sakaigawa, Yasumasa Tashiro, Yoshio Aoki
-
Patent number: 5214191Abstract: 2-Phenylalkanoate esters which are useful as inhibitors of human leukocyte elastase.Type: GrantFiled: May 22, 1990Date of Patent: May 25, 1993Assignee: Cortech, Inc.Inventors: Gary P. Kirschenheuter, Lyle W. Spruce, John C. Cheronis
-
Patent number: 5211879Abstract: This invention provides novel ester compounds represented by the following general formula (1): ##STR1## (wherein R.sup.1 and R.sup.2 are alkyl groups and may be the same or not, A and B are selected from a single bond and --COO--, X is selected from ##STR2## optically active bodies thereof and liquid crystal compositions containing at least one of these compounds.Type: GrantFiled: October 29, 1990Date of Patent: May 18, 1993Assignee: Nippon Mining Co., Ltd.Inventors: Nobuyuki Shiratori, Isa Nishiyama, Atsushi Yoshizawa, Toshihiro Hirai
-
Patent number: 5209867Abstract: Novel derivatives of aromatic carboxylic acid esters which are useful as a dopant for liquid crystal compositions, and smectic liquid crystal compositions containing at least one of said derivatives.Type: GrantFiled: December 30, 1991Date of Patent: May 11, 1993Assignee: Sharp Kabushiki KaishaInventors: Mitsuhiro Koden, Tomoaki Kuratate, Fumiaki Funada
-
Patent number: 5207946Abstract: A liquid crystal compound represented by formula (I): ##STR1## wherein R.sub.1 represents an alkyl group having from 3 to 18 carbon atoms; R.sub.2 represents an alkyl group having from 3 to 18 carbon atoms; X represents ##STR2## (A) and (B) each represents a group selected from the group consisting of ##STR3## and * indicates an optically active center.Type: GrantFiled: July 25, 1990Date of Patent: May 4, 1993Assignee: Showa Shell Sekiyu K.K.Inventors: Koichi Numazawa, Noriko Yamakawa, Yoshiichi Suzuki, Ichiro Kawamura
-
Patent number: 5207947Abstract: Liquid crystal compound of the formula ##STR1## wherein R.sub.1 and R.sub.2 each is a C.sub.1-18 alkyl group or an aralkyl group, R' is a haloalkyl group, X is --0--, --CO--, --COO-- or direct bond, Y is --COO--, --OCO-- or --CH.sub.2 O--, (A) and (B) each is ##STR2## and p and l each is zero or one.Type: GrantFiled: June 11, 1991Date of Patent: May 4, 1993Assignee: Showa Shell Sekiyu Kabushiki KaishaInventors: Yoshiichi Suzuki, Noriko Yamakawa, Yoshihiko Aihara, Hiroyuki Mogamiya, Toru Ooide, Tadaaki Isozaki, Yuvra Negi, Shigenori Sakuma
-
Patent number: 5208388Abstract: 2,2-Difluorocyclopropyl derivatives of the formula ##STR1## in which R represents alkyl, optionally substituted aryl or optionally substituted aralkyl andX represents hydroxymethyl, 2-hydroxyethyl, isocyanato, amino, amino hydrohalide or a radical of the formula --CO--R.sup.1, whereR.sup.1 represents hydrogen, hydroxyl, alkoxy, alkyl, halogen or amino,are intermediates for fungicides.Type: GrantFiled: September 20, 1991Date of Patent: May 4, 1993Assignee: Bayer AktiengesellschaftInventors: Karl-Rudolf Gassen, Bernd Baasner
-
Patent number: 5206411Abstract: Cured products are produced by heating novel 1-arylcyclobutenecarboxylate ester derivatives of N-glycidylamine compounds. The cured products are obtained by applying heat to the ester derivatives, in the presence of or in the absence of added curing agent, and the cured products are crosslinked insoluble solid materials having useful properties characteristic of thermoset polymers.Type: GrantFiled: August 5, 1991Date of Patent: April 27, 1993Assignee: Shell Oil CompanyInventor: Pen-Chung Wang
-
Patent number: 5204020Abstract: Liquid crystal compounds represented by the formula; ##STR1## in which Ra means an alkyl group of 1-20 carbon atoms or an alkoxy group of 1-20 carbon atoms; Rb means an aliphatic alkyl group, a branched alkyl group or an aralkyl group respectively of 1-20 carbon atoms, an alkoxy group of 1-20 carbon atoms, or an alkanoyl methyl group having 1-20 carbon atoms in the alkyl; ##STR2## Z means a fluorinated alkyl or a fluorinated haloalkyl; m is an integer of from 1 to 3; n is an integer of from 0 to 2 where when n is 0, Y is a single bond; and * shows an optically active center, which have a larger spontaneous polarization, high speed of response and good orientation, and show tristable liquid crystal phase.Type: GrantFiled: April 29, 1992Date of Patent: April 20, 1993Assignee: Showa Shell Sekiyu K.K.Inventors: Yoshiichi Suzuki, Hiroyuki Mogamiya, Ichiro Kawamura
-
Patent number: 5204018Abstract: Compounds of the formula ##STR1## wherein n stands for the number 0 or 1; R.sup.1 denotes a group R.sup.3 or R.sup.3 --A.sup.3 --Z.sup.2 -- and R.sup.2 denotes a group R.sup.4 or R.sup.4 --A.sup.4 --Z.sup.3 --; ring A.sup.1 signifies unsubstituted or halogen-, cyano- and/or methyl-substituted 1,4-phenylene in which optionally 1 CH group or 2 CH groups is/are replaced by nitrogen; A.sup.3, A.sup.4 and ring A.sup.2 each independently represent unsubstituted or halogen-, cyano- and/or methyl-substituted 1,4-phenylene in which optionally 1 CH group or 2 CH groups is/are replaced by nitrogen or trans-1,4-cyclohexylene, trans-1,3-dioxane-2,5-diyl, 1-cyano-trans-1,4-cyclohexylene, bicyclo[2.2.2]octane-1,4-diyl, naphthalene-2,6-diyl, tetralin-2,6-diyl or trans-decalin-2,6-diyl; Z.sup.1, Z.sup.2 and Z.sup.3 each independently signify a single covalent bond, --COO--, --OOC--, --CH.sub.2 O--, --OCH.sub.2 --, --CH.tbd.C--, --(CH.sub.2).sub.3 O--, --O(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 -- or the trans form of --CH.Type: GrantFiled: January 22, 1991Date of Patent: April 20, 1993Assignee: Hoffmann-La Roche Inc.Inventor: Stephen Kelly
-
Patent number: 5204019Abstract: 4-Q.sup.1 -4'-Q.sup.2 -2,3-Difluorobiphenyls whereinQ.sup.1 and Q.sup.2 independently of one another are each R or R-A.sup.1 -A.sup.2 -Z in whichR (sic) alkyl having 1-15 C atoms or alkenyl having 3-15 C atoms each of which is unsubstituted or monosubstituted by cyano or at least monosubstituted by fluorine or chlorine, and in which in each case one or two non-adjacent CH.sub.2 groups can also be replaced by --O--, --CO--, --O--CO, --CO--O-- or --O--COO--, (sic) --COO--, --O--CO--, --CH.sub.2 O, --O--CH.sub.2 --, --CH.sub.2 CH.sub.2 -- or a single bond, andA.sup.1 and A.sup.2 independently of one another . . (sic) each 1,4-phenylene which is unsubstituted or substituted by one or two fluorine atoms, and in which one or two CH groups can also be replaced by N, or trans-1,4-cyclohexylene wherein one or two non-adjacent CH.sub.2 groups can also be replaced by --O--, and one of the two groups A.sup.1 and A.sup.2 can also be a single bond,subject to the proviso that Z is --CO--O, --O--CO--, --CH.sub.2 O--, --OCH.Type: GrantFiled: May 15, 1989Date of Patent: April 20, 1993Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Volker Reiffenrath, Joachim Krause, Andreas Wachtler, Georg Weber, Ulrich Finkenzeller, David Coates, Ian C. Sage, Simon Greenfield, George W. Gray, Michael Hird, David Lacey, Kenneth J. Toyne
-
Patent number: 5196567Abstract: Biphenylylpropionic acid derivatives of the formula: ##STR1## wherein R is an alkylcarbonyloxyalkyl group or an alkenylcarbonyloxyalkyl group having the formula: ##STR2## wherein R.sup.1 is a lower alkyl group having 1 to 5 carbon atoms and R.sup.2 is an alkyl group having 1 to 15 carbon atoms or an alkenyl group having 2 to 8 carbon atoms, or a lactone having the formula: ##STR3## wherein R.sup.3 and R.sup.4 are hydrogen atom or a lower alkyl group having 1 to 2 carbon atoms, and n is an integer of 1 or 2. The compounds have excellent anti-inflammatory, analgesic and antipyretic activities. Moreover, the compounds have no irritation, rapid and long-acting, and high safety margin.Type: GrantFiled: June 9, 1988Date of Patent: March 23, 1993Assignee: Kaken Pharmaceutical Co., Ltd.Inventors: Katsuhiro Uchida, Shozo Masumoto, Masao Tohno, Mitsuo Mimura, Makoto Okumura
-
Patent number: 5188762Abstract: A mesomorphic compound represented by the following formula (I): ##STR1## wherein R.sub.1 denotes a linear or branched alkyl group having 2-16 carbon atoms capable of including one or two non-neighboring methylene groups which can be replaced with ##STR2## and capable of including fluorine substituted for hydrogen; A denotes --A.sub.1 -- or --A.sub.1 --A.sub.2 -- and B denotes --B.sub.1 -- or --B.sub.1 --B.sub.2 -- wherein A.sub.1, A.sub.2, B.sub.1 and B.sub.2 respectively denote ##STR3## wherein Y.sub.1 and Y.sub.2 respectively denote H, F, Cl, Br, --CH.sub.3, --CN or --CF.sub.3 ; Z.sub.1 and Z.sub.2 respectively denote ##STR4## Z.sub.3 denotes ##STR5## R.sub.2, R.sub.3 and R.sub.4 respectively denote a linear or branched alkyl group having 1-16 carbon atoms including a methylene group which can be replaced with ##STR6## with proviso that it is not adjacent to the silicon atom; p and q are respectively 0 or 1 with proviso that p+q is 0 or 1; and n is an integer of 1-12.Type: GrantFiled: May 20, 1991Date of Patent: February 23, 1993Assignee: Canon Kabushiki KaishaInventors: Takashi Iwaki, Takao Takiguchi, Takeshi Togano, Yoko Yamada, Shinichi Nakamura
-
Patent number: 5188759Abstract: The invention relates to a liquid crystalline medium having at least two components, where at least one component is a haloacetylene derivatives of the formula IR.sup.1 --A.sup.1 --Z.sup.1 --(A.sup.2 --Z.sup.2).sub.m --A.sup.3 --C.tbd.C--X IwhereinR.sup.1 is an alkyl or alkenyl radical having up to 15 carbon atoms which is unsubstituted or monosubstituted by CN, halogen or CF.sub.3, or such a radical wherein one or more CH.sub.2 groups is replaced, in each case independently of one another, by --S--, --O--, ##STR1## --CO--, --CO--O--, --O--CO-- or --O--CO--O-- in such a manner that sulfur and/or oxygen atoms are not linked directly to one another,A.sup.1, A.sup.2 and A.sup.3, in each case independently of one another, are(a) a trans-1,4-cyclohexylene radical or --S-- one or more non-adjacent CH.sub.Type: GrantFiled: February 1, 1991Date of Patent: February 23, 1993Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Ekkehard Bartmann, Reinhard Hittich, Herbert Plach, Ulrich Finkenzeller
-
Patent number: 5184847Abstract: Ferrelectric chiral smetic liquid crystal compound are provided which have the formula, for example ##STR1## wherein R is a C.sub.1-20 alkyl group.Type: GrantFiled: November 4, 1991Date of Patent: February 9, 1993Assignee: Showa Shell Sekiyu Kabushiki KaishaInventors: Yoshiichi Suzuki, Hiroyuki Mogamiya, Ichiro Kawamura